JP2009529047A5 - - Google Patents
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- JP2009529047A5 JP2009529047A5 JP2008558335A JP2008558335A JP2009529047A5 JP 2009529047 A5 JP2009529047 A5 JP 2009529047A5 JP 2008558335 A JP2008558335 A JP 2008558335A JP 2008558335 A JP2008558335 A JP 2008558335A JP 2009529047 A5 JP2009529047 A5 JP 2009529047A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrazolo
- phenyl
- yloxy
- fluorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 84
- 125000000623 heterocyclic group Chemical group 0.000 claims 54
- -1 cyclopropylidene Chemical group 0.000 claims 51
- 125000001072 heteroaryl group Chemical group 0.000 claims 46
- 125000003118 aryl group Chemical group 0.000 claims 37
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 28
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 28
- 229910052801 chlorine Inorganic materials 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052731 fluorine Inorganic materials 0.000 claims 25
- 229910052794 bromium Inorganic materials 0.000 claims 24
- 125000004452 carbocyclyl group Chemical group 0.000 claims 23
- 229910005965 SO 2 Inorganic materials 0.000 claims 21
- 229910052740 iodine Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 125000004429 atoms Chemical group 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000005418 aryl aryl group Chemical group 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000005842 heteroatoms Chemical group 0.000 claims 5
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- QAVYDPMCCPMIMA-UHFFFAOYSA-N 1-(1,3-benzoxazol-2-yl)-N-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]cyclopropane-1-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4(CC4)C=4OC5=CC=CC=C5N=4)=CC=3)F)=C12 QAVYDPMCCPMIMA-UHFFFAOYSA-N 0.000 claims 1
- IKSRPHLQEGXXGS-UHFFFAOYSA-N 1-N'-(4-fluorophenyl)-1-N'-[4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]cyclopropane-1,1-dicarboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C=C1)=CC=C1N(C=1C=CC(F)=CC=1)C(=O)C1(C(N)=O)CC1 IKSRPHLQEGXXGS-UHFFFAOYSA-N 0.000 claims 1
- YTMOLVGYLBFYEJ-UHFFFAOYSA-N 1-N'-[3-fluoro-4-[[3-[2-(4-methylpiperazin-1-yl)ethyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1CN(C)CCN1CCC1=NNC2=NC=CC(OC=3C(=CC(=CC=3)N(C(=O)C3(CC3)C(N)=O)C=3C=CC(F)=CC=3)F)=C12 YTMOLVGYLBFYEJ-UHFFFAOYSA-N 0.000 claims 1
- RQDGTOYZOBSJDZ-UHFFFAOYSA-N 1-N'-[3-fluoro-4-[[3-[3-(methylcarbamoyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound CNC(=O)C1=CC=CC(C=2C3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC(F)=CC=4)F)C=CN=C3NN=2)=C1 RQDGTOYZOBSJDZ-UHFFFAOYSA-N 0.000 claims 1
- LHMHIVIVMVOYLE-UHFFFAOYSA-N 1-N'-[3-fluoro-4-[[3-[5-[(4-methylpiperazin-1-yl)methyl]furan-3-yl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1CN(C)CCN1CC1=CC(C=2C3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC(F)=CC=4)F)C=CN=C3NN=2)=CO1 LHMHIVIVMVOYLE-UHFFFAOYSA-N 0.000 claims 1
- FXUKPCLDNDAEHQ-UHFFFAOYSA-N 1-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-pyridin-2-ylurea Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)NC1=CC=CC=N1 FXUKPCLDNDAEHQ-UHFFFAOYSA-N 0.000 claims 1
- DUJXTXVAJACGSD-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-N-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]acetamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)CC=4OC5=CC=CC=C5N=4)=CC=3)F)=C12 DUJXTXVAJACGSD-UHFFFAOYSA-N 0.000 claims 1
- CBFAVFULWUWDGH-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[2-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]pyrimidin-5-yl]-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(N=C1)=NC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 CBFAVFULWUWDGH-UHFFFAOYSA-N 0.000 claims 1
- CAHHJGBCLQZQOM-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[(3-piperazin-1-yl-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 CAHHJGBCLQZQOM-UHFFFAOYSA-N 0.000 claims 1
- SPCVWZIVKSEQKR-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[(3-piperidin-4-yl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 SPCVWZIVKSEQKR-UHFFFAOYSA-N 0.000 claims 1
- FUDWBRLWTYHGBF-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[(3-pyrazol-4-ylidene-1,2-dihydropyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(=C5C=NN=C5)NNC=4N=CC=3)=CC=2)=CC=N1 FUDWBRLWTYHGBF-UHFFFAOYSA-N 0.000 claims 1
- CLLRKPIKZGXPNG-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[(3-pyridin-3-yl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=NC=CC=5)=NNC=4N=CC=3)=CC=2)=CC=N1 CLLRKPIKZGXPNG-UHFFFAOYSA-N 0.000 claims 1
- RWTYLSUDJBYXHX-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(1,2,3,6-tetrahydropyridin-4-yl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5CCNCC=5)=NNC=4N=CC=3)=CC=2)=CC=N1 RWTYLSUDJBYXHX-UHFFFAOYSA-N 0.000 claims 1
- RCERBRZFXRIRIT-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(1-piperidin-4-ylpyrazol-4-yl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C5=CN(N=C5)C5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 RCERBRZFXRIRIT-UHFFFAOYSA-N 0.000 claims 1
- IDWKWRRAUUARSD-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(4-piperazin-1-ylphenyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)N5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 IDWKWRRAUUARSD-UHFFFAOYSA-N 0.000 claims 1
- UUMQLVCYOXAKEC-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(4-propan-2-ylpiperazine-1-carbonyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C(C)C)CCN1C(=O)C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 UUMQLVCYOXAKEC-UHFFFAOYSA-N 0.000 claims 1
- SWFJTRDTGFQNNG-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(4-pyrrolidin-1-ylpiperidin-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5CCC(CC5)N5CCCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 SWFJTRDTGFQNNG-UHFFFAOYSA-N 0.000 claims 1
- ARWJOZPFUSMKES-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(piperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 ARWJOZPFUSMKES-UHFFFAOYSA-N 0.000 claims 1
- LMNNRVRRULMESK-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(piperidin-4-ylmethyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(CC5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 LMNNRVRRULMESK-UHFFFAOYSA-N 0.000 claims 1
- YKYQEFHSHJBTAO-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(pyrrolidin-3-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 YKYQEFHSHJBTAO-UHFFFAOYSA-N 0.000 claims 1
- DJFGVFOSGODYGW-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 DJFGVFOSGODYGW-UHFFFAOYSA-N 0.000 claims 1
- QYHCRZYLKDBYKA-HSZRJFAPSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-[(2R)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5[C@H](CCC5)CN5CCCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 QYHCRZYLKDBYKA-HSZRJFAPSA-N 0.000 claims 1
- SICGKDJUHCIWIA-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[6-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]pyridin-3-yl]-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(N=C1)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 SICGKDJUHCIWIA-UHFFFAOYSA-N 0.000 claims 1
- HIGVKGMGGRNDOG-UHFFFAOYSA-N 2-(cyclohexylmethyl)-5-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)C(=O)N5CCOCC5)=NNC=4N=CC=3)=CC=2)C(=O)N(C)C=1CC1CCCCC1 HIGVKGMGGRNDOG-UHFFFAOYSA-N 0.000 claims 1
- ZEHHLYMHSQRGNJ-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-5-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCC1CC1 ZEHHLYMHSQRGNJ-UHFFFAOYSA-N 0.000 claims 1
- ZICAZXCZHGFFQS-UHFFFAOYSA-N 2-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]anilino]-N-(4-fluorophenyl)pyridine-3-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC=4C(=CC=CN=4)C(=O)NC=4C=CC(F)=CC=4)=CC=3)F)=C12 ZICAZXCZHGFFQS-UHFFFAOYSA-N 0.000 claims 1
- LDUGMDDJWJCONU-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=C1 LDUGMDDJWJCONU-UHFFFAOYSA-N 0.000 claims 1
- BIQZYBBVDZAVPZ-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[[3-(4-fluorophenyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C=4C(C=5C=CC(F)=CC=5)=NNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=CC=C1 BIQZYBBVDZAVPZ-UHFFFAOYSA-N 0.000 claims 1
- WFHKRJMKNVHPAS-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)C(=O)N5CCOCC5)=NNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=CC=C1 WFHKRJMKNVHPAS-UHFFFAOYSA-N 0.000 claims 1
- UBAWQZFXFMKRDQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-fluoro-4-[(3-piperazin-1-yl-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C2(C(=O)NC=3C=C(F)C(OC=4C=5C(N6CCNCC6)=NNC=5N=CC=4)=CC=3)CC2C1 UBAWQZFXFMKRDQ-UHFFFAOYSA-N 0.000 claims 1
- CWFPETGAOXZZMK-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]pyrimidin-4-one Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(Cl)C=C1 CWFPETGAOXZZMK-UHFFFAOYSA-N 0.000 claims 1
- UWJXMGKPTGPXPO-UHFFFAOYSA-N 3-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1,4-dihydroquinazolin-2-one Chemical compound C1C2=CC=CC=C2NC(=O)N1C(C=C1F)=CC=C1OC1=C2C(C)=NNC2=NC=C1 UWJXMGKPTGPXPO-UHFFFAOYSA-N 0.000 claims 1
- LFXAGJXLAYLHGR-UHFFFAOYSA-N 4-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(4-propan-2-ylpiperazine-1-carbonyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1CN(C(C)C)CCN1C(=O)C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 LFXAGJXLAYLHGR-UHFFFAOYSA-N 0.000 claims 1
- DQPHFHDECJHGPS-UHFFFAOYSA-N 4-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(piperidin-4-ylmethyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(CC5CCNCC5)=NNC=4N=CC=3)=CC=2)=NC=C1 DQPHFHDECJHGPS-UHFFFAOYSA-N 0.000 claims 1
- WTWMYVHNSSMCSG-UHFFFAOYSA-N 4-(4-fluorophenyl)-N-[3-fluoro-4-[[3-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 WTWMYVHNSSMCSG-UHFFFAOYSA-N 0.000 claims 1
- LAPVFEUWCXXCQS-UHFFFAOYSA-N 4-[4-[2-fluoro-4-[[1-[(4-fluorophenyl)carbamoyl]cyclopropanecarbonyl]amino]phenoxy]-2H-pyrazolo[3,4-b]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4(CC4)C(=O)NC=4C=CC(F)=CC=4)=CC=3)F)=C12 LAPVFEUWCXXCQS-UHFFFAOYSA-N 0.000 claims 1
- SOQIEUZYPSJOKY-UHFFFAOYSA-N 4-benzyl-N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=NC=CN1CC1=CC=CC=C1 SOQIEUZYPSJOKY-UHFFFAOYSA-N 0.000 claims 1
- KDJYKPDYWKWGKJ-UHFFFAOYSA-N 4-benzyl-N-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C=1C=C(OC=2C=3C(C=4C=CC(=CC=4)C(=O)N4CCOCC4)=NNC=3N=CC=2)C(F)=CC=1NC(=O)C(C1=O)=NC=CN1CC1=CC=CC=C1 KDJYKPDYWKWGKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- PPPLBGVCEQCLFW-UHFFFAOYSA-N N-[2,3-difluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1F)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 PPPLBGVCEQCLFW-UHFFFAOYSA-N 0.000 claims 1
- AKXLXFHSBDEXOA-UHFFFAOYSA-N N-[2,5-difluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC(F)=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 AKXLXFHSBDEXOA-UHFFFAOYSA-N 0.000 claims 1
- VIEWECCEKTXACR-UHFFFAOYSA-N N-[2-chloro-5-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC(Cl)=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 VIEWECCEKTXACR-UHFFFAOYSA-N 0.000 claims 1
- XLNPLMDBUKUWRC-UHFFFAOYSA-N N-[2-chloro-5-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=C(Cl)C=3)F)=C12 XLNPLMDBUKUWRC-UHFFFAOYSA-N 0.000 claims 1
- GZIYTHBKELBBCJ-UHFFFAOYSA-N N-[2-chloro-5-methyl-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound ClC=1C=C(OC=2C=3C(C=4C=CC(=CC=4)C(=O)N4CCOCC4)=NNC=3N=CC=2)C(C)=CC=1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 GZIYTHBKELBBCJ-UHFFFAOYSA-N 0.000 claims 1
- SRJUSQCMBAUMJH-UHFFFAOYSA-N N-[3-fluoro-4-(1-methyl-3-phenylpyrazolo[3,4-b]pyridin-4-yl)oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C12=C(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)C=CN=C2N(C)N=C1C1=CC=CC=C1 SRJUSQCMBAUMJH-UHFFFAOYSA-N 0.000 claims 1
- YUGBUKDMWDFNCT-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1=CC=C(F)C=C1 YUGBUKDMWDFNCT-UHFFFAOYSA-N 0.000 claims 1
- AIMIMKZRQBMDNL-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)CCN1C1=CC=C(F)C=C1 AIMIMKZRQBMDNL-UHFFFAOYSA-N 0.000 claims 1
- AGJFHMIXRRVAML-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C1=CC=CN(C)C1=O AGJFHMIXRRVAML-UHFFFAOYSA-N 0.000 claims 1
- IQEWMAABOBFSHI-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1-methyl-2-oxopyrrolidine-3-carboxamide Chemical compound O=C1N(C)CCC1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1C(C)=NN2 IQEWMAABOBFSHI-UHFFFAOYSA-N 0.000 claims 1
- GOQLLKXDNDUHSB-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 GOQLLKXDNDUHSB-UHFFFAOYSA-N 0.000 claims 1
- GHSFYNJGDFMLJF-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-methyl-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C1=CC=NN(C)C1=O GHSFYNJGDFMLJF-UHFFFAOYSA-N 0.000 claims 1
- FACGQBFORBZHTQ-UHFFFAOYSA-N N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-oxopyrrolidine-3-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C1CCNC1=O FACGQBFORBZHTQ-UHFFFAOYSA-N 0.000 claims 1
- UXTVSZGDDHVMEA-UHFFFAOYSA-N N-[3-fluoro-4-[(3-morpholin-4-yl-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5CCOCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 UXTVSZGDDHVMEA-UHFFFAOYSA-N 0.000 claims 1
- UPHNONJFFAIKJN-UHFFFAOYSA-N N-[3-fluoro-4-[3-(4-fluorophenyl)-1-methylpyrazolo[3,4-b]pyridin-4-yl]oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C12=C(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)C=CN=C2N(C)N=C1C1=CC=C(F)C=C1 UPHNONJFFAIKJN-UHFFFAOYSA-N 0.000 claims 1
- RUUBBFCLUPQERU-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(1-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-5-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1C2N(C)CCC2CN1C(C=12)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 RUUBBFCLUPQERU-UHFFFAOYSA-N 0.000 claims 1
- SVVDUAKUJFHGJD-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(1-methylimidazol-2-yl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound CN1C=CN=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 SVVDUAKUJFHGJD-UHFFFAOYSA-N 0.000 claims 1
- LRPRDPICHSVJML-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(1-methylpiperidin-4-yl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCC1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 LRPRDPICHSVJML-UHFFFAOYSA-N 0.000 claims 1
- IIYYUWQAKQROIQ-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(1-methylpyrazol-4-yl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=NN(C)C=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 IIYYUWQAKQROIQ-UHFFFAOYSA-N 0.000 claims 1
- RFSQNGPJNPNDCK-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(2-hydroxyethyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(CCO)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 RFSQNGPJNPNDCK-UHFFFAOYSA-N 0.000 claims 1
- QTIVYMJAXPRBIO-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(2-methylphenyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound CC1=CC=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 QTIVYMJAXPRBIO-UHFFFAOYSA-N 0.000 claims 1
- GQJDUMOWYYLAJY-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(3-methylimidazol-4-yl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound CN1C=NC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 GQJDUMOWYYLAJY-UHFFFAOYSA-N 0.000 claims 1
- LMZCBIGNHHETEY-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(4-fluorophenyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 LMZCBIGNHHETEY-UHFFFAOYSA-N 0.000 claims 1
- OQNDPYGGJGSYDB-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 OQNDPYGGJGSYDB-UHFFFAOYSA-N 0.000 claims 1
- CXDZBCUUEUIHGN-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxo-2-pyridin-2-ylpyridazine-4-carboxamide Chemical compound C1CN(C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5N=CC=CC=5)N=CC=4)=O)=CC=3)F)=C12 CXDZBCUUEUIHGN-UHFFFAOYSA-N 0.000 claims 1
- UGJBEVKDQMSDPR-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(4-methylpiperazine-1-carbonyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 UGJBEVKDQMSDPR-UHFFFAOYSA-N 0.000 claims 1
- RNQJUHKUZGBCNR-UHFFFAOYSA-N N-[3-fluoro-4-[[3-(oxan-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CCOCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 RNQJUHKUZGBCNR-UHFFFAOYSA-N 0.000 claims 1
- MQYOGDYNVXAYQA-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-(4-fluorophenyl)-2-oxoazepane-3-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4C(N(C=5C=CC(F)=CC=5)CCCC4)=O)=CC=3)F)=C12 MQYOGDYNVXAYQA-UHFFFAOYSA-N 0.000 claims 1
- ZTESXMAKJAHPAE-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CC=4)=O)=CC=3)F)=C12 ZTESXMAKJAHPAE-UHFFFAOYSA-N 0.000 claims 1
- MZABKBDFFVWSPY-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 MZABKBDFFVWSPY-UHFFFAOYSA-N 0.000 claims 1
- UONAEXMYVRONMC-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxo-2-pyridin-2-ylpyridazine-4-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5N=CC=CC=5)N=CC=4)=O)=CC=3)F)=C12 UONAEXMYVRONMC-UHFFFAOYSA-N 0.000 claims 1
- AYWOXSRJQVYOIJ-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-phenylbenzamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C=C(C=CC=4)C=4C=CC=CC=4)=CC=3)F)=C12 AYWOXSRJQVYOIJ-UHFFFAOYSA-N 0.000 claims 1
- LXJSRWDKZGPIHC-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-4-(4-fluorophenyl)-3-oxopyrazine-2-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 LXJSRWDKZGPIHC-UHFFFAOYSA-N 0.000 claims 1
- LTGITATXWVOHAZ-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(3-hydroxycyclohexyl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1C(O)CCCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 LTGITATXWVOHAZ-UHFFFAOYSA-N 0.000 claims 1
- JBMUNMIFFUSBKL-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-4-(4-fluorophenyl)-3-oxopyrazine-2-carboxamide Chemical compound CN1C(C2)CCC1CC2NC(C=12)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=NC=CN1C1=CC=C(F)C=C1 JBMUNMIFFUSBKL-UHFFFAOYSA-N 0.000 claims 1
- JOPQLIAQRRMRSE-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[4-(2-methoxyethyl)piperazin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(CCOC)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 JOPQLIAQRRMRSE-UHFFFAOYSA-N 0.000 claims 1
- BTYJBHVLVJLKTN-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[4-(methylamino)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CC(NC)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 BTYJBHVLVJLKTN-UHFFFAOYSA-N 0.000 claims 1
- IVTRVOWFNZWCSL-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[4-(methylcarbamoyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-methyl-2-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4C(N(C)CC4)=O)=CC=3)F)=C12 IVTRVOWFNZWCSL-UHFFFAOYSA-N 0.000 claims 1
- VIZFVZDWCKQICZ-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)C(=O)N5CCOCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 VIZFVZDWCKQICZ-UHFFFAOYSA-N 0.000 claims 1
- QADUINPLQNGMAM-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-4-methyl-3-oxopyrazine-2-carboxamide Chemical compound O=C1N(C)C=CN=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1C(C=1C=CC(=CC=1)C(=O)N1CCOCC1)=NN2 QADUINPLQNGMAM-UHFFFAOYSA-N 0.000 claims 1
- BUAHSOJGMDGSOU-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[[1-(2-fluoroethyl)piperidin-4-yl]amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CCF)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 BUAHSOJGMDGSOU-UHFFFAOYSA-N 0.000 claims 1
- NFUHTWNHZCURNS-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[[1-(2-hydroxyethyl)piperidin-4-yl]amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(CCO)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 NFUHTWNHZCURNS-UHFFFAOYSA-N 0.000 claims 1
- ZXELOZQYQABKCF-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[[1-(2-methoxyethyl)piperidin-4-yl]amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CCOC)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 ZXELOZQYQABKCF-UHFFFAOYSA-N 0.000 claims 1
- GAHXXXBESXMEQG-UHFFFAOYSA-N N-[3-fluoro-4-[[3-[methyl-(1-methylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound N=1NC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C2C=1N(C)C1CCN(C)CC1 GAHXXXBESXMEQG-UHFFFAOYSA-N 0.000 claims 1
- NAUDWLUUSFPKRT-UHFFFAOYSA-N N-[4-[[3-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5CC6CNCC6C5)=NNC=4N=CC=3)=CC=2)=CC=N1 NAUDWLUUSFPKRT-UHFFFAOYSA-N 0.000 claims 1
- SQQPXGFYGGHUCL-UHFFFAOYSA-N N-[4-[[3-(3-chlorophenyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=C(Cl)C=CC=5)=NNC=4N=CC=3)=CC=2)=CC=N1 SQQPXGFYGGHUCL-UHFFFAOYSA-N 0.000 claims 1
- JXERQFCEXBMAMP-UHFFFAOYSA-N N-[4-[[3-[(1-ethylpiperidin-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(CC)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 JXERQFCEXBMAMP-UHFFFAOYSA-N 0.000 claims 1
- ZHJSJSQWLMHTGQ-UHFFFAOYSA-N N-[4-[[3-[(1-ethylpiperidin-4-yl)methyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-4-(4-fluorophenyl)-3-oxopyrazine-2-carboxamide Chemical compound C1CN(CC)CCC1CC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 ZHJSJSQWLMHTGQ-UHFFFAOYSA-N 0.000 claims 1
- MYDPMRDRYKLTGU-HXUWFJFHSA-N N-[4-[[3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1[C@H](N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 MYDPMRDRYKLTGU-HXUWFJFHSA-N 0.000 claims 1
- RQLHHRJWUPJIFN-UHFFFAOYSA-N N-[4-[[3-[2-[(dimethylamino)methyl]piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound CN(C)CC1CCCCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 RQLHHRJWUPJIFN-UHFFFAOYSA-N 0.000 claims 1
- DFSOIXFJBFCGHY-UHFFFAOYSA-N N-[4-[[3-[3-(dimethylamino)propylamino]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(NCCCN(C)C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 DFSOIXFJBFCGHY-UHFFFAOYSA-N 0.000 claims 1
- QOENHNXLNBSTKP-UHFFFAOYSA-N N-[4-[[3-[4-(dimethylamino)phenyl]-2H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 QOENHNXLNBSTKP-UHFFFAOYSA-N 0.000 claims 1
- NEFBUIHSRZKYJD-UHFFFAOYSA-N N-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 NEFBUIHSRZKYJD-UHFFFAOYSA-N 0.000 claims 1
- UGTRUZIPOLZFMT-UHFFFAOYSA-N N-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-3-(4-fluorophenyl)-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C45C(C4)CN(C5=O)C=4C=CC(F)=CC=4)=CC=3)F)=C12 UGTRUZIPOLZFMT-UHFFFAOYSA-N 0.000 claims 1
- VJOLBFHEBPXHII-UHFFFAOYSA-N N-[5-chloro-2-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)Cl)=CC(F)=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 VJOLBFHEBPXHII-UHFFFAOYSA-N 0.000 claims 1
- XYVCJSMWTFHTQN-UHFFFAOYSA-N N-benzyl-N-[3-fluoro-4-[(3-methyl-2H-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]acetamide Chemical compound C=1C=C(OC=2C=3C(C)=NNC=3N=CC=2)C(F)=CC=1N(C(=O)C)CC1=CC=CC=C1 XYVCJSMWTFHTQN-UHFFFAOYSA-N 0.000 claims 1
- YXCUZSXWFOTQIS-UHFFFAOYSA-N [3-[[4-[2-fluoro-4-[[2-(4-fluorophenyl)-3-oxopyridazine-4-carbonyl]amino]phenoxy]-1H-pyrazolo[3,4-b]pyridin-3-yl]amino]cyclohexyl] 2,2,2-trifluoroacetate Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CC(CCC5)OC(=O)C(F)(F)F)=NNC=4N=CC=3)=CC=2)=CC=N1 YXCUZSXWFOTQIS-UHFFFAOYSA-N 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000001717 carbocyclic compounds Chemical class 0.000 claims 1
- FEHLGOYZDFFMND-UHFFFAOYSA-N cyclopropane-1,1-dicarboxamide Chemical compound NC(=O)C1(C(N)=O)CC1 FEHLGOYZDFFMND-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- DCVLOIOMXXTLHE-UHFFFAOYSA-N methyl 4-[2-fluoro-4-[[2-(4-fluorophenyl)-3-oxopyridazine-4-carbonyl]amino]phenoxy]-2H-pyrazolo[3,4-b]pyridine-3-carboxylate Chemical compound C=12C(C(=O)OC)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 DCVLOIOMXXTLHE-UHFFFAOYSA-N 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 0 CN(***C1(*)C(C(*)(*)**)=*)C1=C Chemical compound CN(***C1(*)C(C(*)(*)**)=*)C1=C 0.000 description 1
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- 2007-03-06 JP JP2008558335A patent/JP2009529047A/ja active Pending
- 2007-03-06 KR KR1020087024415A patent/KR20080110783A/ko not_active Application Discontinuation
- 2007-03-06 US US11/714,342 patent/US7723330B2/en not_active Expired - Fee Related
- 2007-03-06 MX MX2008011220A patent/MX2008011220A/es not_active Application Discontinuation
- 2007-03-06 AU AU2007224020A patent/AU2007224020A1/en not_active Abandoned
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- 2007-03-06 CA CA002645137A patent/CA2645137A1/en not_active Abandoned
- 2007-03-06 BR BRPI0708615-6A patent/BRPI0708615A2/pt not_active Application Discontinuation
- 2007-03-07 AR ARP070100948A patent/AR059887A1/es unknown
- 2007-03-07 CL CL2007000601A patent/CL2007000601A1/es unknown
- 2007-03-07 TW TW096107890A patent/TW200800996A/zh unknown
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2008
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- 2008-09-19 MA MA31254A patent/MA31339B1/fr unknown
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2010
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